Wednesday, November 27, 2019

On the Road

By Brenda

For many of us. crossdressing or femulating offers us a chance to express ourselves. Unless you have outed yourself to your spouse or family, it can be very difficult to get better at it by practicing your makeup and presentation skills.

Business travel offers an ideal environment to enjoy the art of crossdressing without the fear of getting caught by those who know you personally.

Airlines have made it more problematic with bag fees to accommodate “her luggage.” With careful packing, you can get away with just a carry-on, but that would entail a TSA pass through that could  pose a problem. Car travel offers a trunk full of shoes to choose from, but departing en femme could be risky. Hotel desk agents typically don’t really care how you check in, so a driveway to check in adventure is very possible. [Stana adds, on countless occasions, I have checked-in in male mode and checked-out in girl mode (or vice versa) and it has never been an issue.]

If you plan ahead, there are local crossdresser groups that have outings that might coincide with your stay to allow you to venture out with others limiting any anxiety of where to go or what to do.

Even if you cannot go fully dressed, the hotel offers a chance after a day of business meetings to practice your makeup skills, which is crucial to proper presentation. I find that even civilians can get the foundation color wrong, but they can get help from the cosmetics counter. I am still not confident with trying that in either gender mode, so I have used my colors when I had a proper makeover done and have experimented when that base color was discontinued. I was able to try a few wig styles and makeup ideas to arrive at a look I felt good about.

Many large cities offer makeover services and I urge you to try them because you will have a very safe environment to learn from a master in the art, offer proper color choices and have a better wig collection to choose from. You must have an agenda of where to go afterwards. ATM machines are popular and shopping malls are safe. You will cruise right by the front desk when you get back to your hotel and sashaying up to your room is easy and will bring great confidence.

I took the plunge for a proper makeover after being disappointed so many times by my lack of skills in makeup application. This is key to femulating well. So pay attention when getting this done and even take notes on the actual products being used.

I was so thrilled with how I looked and felt, I ventured out in the world with my held up high. However, I was very scared about getting caught in my neighbourhood. Doing this in a far off city would have been ideal. The makeover process really turned things around for me because I was able to really really see how well I could look giving me a lot of confidence to venture out as truly myself.

Some Tips

Makeup is key and takes practice. Press-on nails are your friend

TSA has not been an issue... not even asking me why I have four pairs of heels in my carry on. But for makeup, the checked bag will have to be planned.

Dressing your age or your chosen persona is also important to blending in. I feel comfortable as a middle-aged business woman in a two-piece dress suit with suitable heels. Leave the stripper heels and shiny PVC dress in your room, as it will attract unwanted attention.

I enjoy cooler weather when my foundation doesn’t run and wearing more layers makes me too hot. I don’t know how woman really do it in hot muggy weather.

Explore the local thrift shops in both modes to find things to wear. I have found the staff to be helpful and even complimentary. And shopping malls are so busy these days, no one will be on the lookout for crossdressers, so you can enjoy your time without fear.

Local support groups are also wonderful. I did enjoy a night out for dinner at a trans-friendly restaurant and wasn’t worried about trying to fake my voice. I had a great time and really felt myself.

Of course, in-room femulations don't require much in the way of makeup, but at least have nails and lipstick to complete your look.

I have ventured out and felt so good that I rode the subway around the city and realized that no one took particular interest of a woman making her way home from work after a bit of shopping.

On one trip, I was able to a experience a rainbow and not only did I feel sexy, but also felt truly as myself – not as a crossdresser, but as someone that could live life this way full-time. My goal is to live my life as Brenda for several days as a start.

Bon voyage en femme!

Source: New York & Company
Wearing New York & Company

Bill Kaulitz
Bill Kaulitz


  1. Wonderful post. Back when I was doing a fair amount of business travel before we became empty nesters I always had an assortment of 'travel bags' stashed around the house. Each bag held a full outfit with some makeup, wig, dresses, shoes, etc. I spent many evenings in hotels and on occasion got out to a bar or restaurant. This depended on the town and whether I had evening business to attend to which was often the case.

  2. It's often possible to get a makeover at a MAC location. Check locations where you're going to travel and make a makeover reservation. The really good deal at MAC is that the full makeover is included with the purchase of $60 of MAC products. Their people do great work!

  3. I remember with great affection a trip to France, four days when I could properly be Paula without having to worry about other people, or having to revert to "him" before getting home. Back in 2011 this was my first real adventure being truly myself, now I no longer have to life that double life.

  4. Hotels can be such a refuge for anonymously practicing the 'forbidden'. My first revelation that hotels were for more than sleeping, was my first read of J.D Salanger's 'Catcher In The Rye' (1951).
    Holden Caufield checks in to a seedy hotel only to witness various other hotel occupants, across the way, each involved in their own versions of self expression....
    "In one room is a transvestite, a distinguished-looking older gentleman enjoying himself as he dons silk stockings, high heels, a bra, a corset, and a black evening dress."
    One has to wonder Salingers' personal motivation for including such a visual vignette.
    DO draw the drapes, unless you also have exhibitionist tendencies....

  5. Hello Brenda

    I love your post as I too am a dressed up in my hotel room.

    Business Travel has allowed me to enjoy my femininity and meet others.

    My best times enfemme were enjoying myself at the casino.

    Shopping at Target and Dress Barn and of course Payless

    So the joy of business travel is knowing for that time I can be myself in a private setting and go on out and about with total freedom.

    I am going to echo your concept of not dressing like white trash but to pass as a woman with class.